Come cruise the Boston Harbor Islands

Winthrop, MA, United States 5.0/5 stars 4 reviews


With Captain
Up to 6



The Boat

Model: Downeast Cruiser
Type: Power
Year: 2001
Length: 35 ft.
Passenger Capacity: Up to 6
Sleeps: 6
Rooms: 2
Fuel Type: Diesel
Fuel Capacity: 200
Horsepower: 350


Chart Plotter
Depth Finder
Fish Finder
Rod Holders
Stereo Aux Input
Swim Ladder
Vhf Radio
Tubes Inflatables

Boat Rules

1 week advance notice required, excludes weekends and holidays


Cancellation Policy

Free cancellation up to 5 days from trip start and 50% refund for cancellations within 2-5 days from trip start. Cancellations within 2 days of trip start date are non-refundable.
+ service fees

You won't be charged yet


- or -
Captain Info
If requested, the owner can provide a list of available captains for bareboat charter or the renter can use their own qualified captain. If the boat is being time chartered, the owner will provide the Captain.

Meet Chris

Aboard since 2014
Response Rate
< 12 hours
Response Time


5.0/5 stars

  • We had a fantastic day with Chris! He was accommodating to exactly what we wanted to do that day and was super knowledgeable about the Harbor island we visited as well as the surrounding area. His boat really is equipped with all you could need - a kayak, paddleboard, noodles, and a cooler. We had a terrific time and could not recommend him more if you're looking for a great day trip.

  • We had an amazing time with Chris! So thankful for such a beautiful day exploring the harbor islands area. His boat is equipped with everything you need and more: a cooler, stand up paddle board, swimming noodles and a kayak! We had a blast getting out in the water on a warm sunny day, and then exploring Lovells Island with Chris as our tour guide.

  • Chris was awesome! He customized our trip to see the things we enjoy--lighthouses and seals--and included taking us to a great island where we picnicked. He gave us a good tour of this island and its old military bunkers. We were the only ones there, which was very cool to not be around tourists and crowds. Chris also included a kayak and paddleboard on the boat for us.

    Then we were coming up to a lighthouse, Chris radio'd ahead, and the next thing you know the owner invited us up—113' feet up. It was a highlight of the day. Another highlight was taking us to Hull Island to a local bar on the shore with THE BEST Bloody Mary's ever!!!! Chris keeps lobster pots, so let him know ahead of time, and he'll bate them, and grill them on the beach of one of the islands. He brings the grill!

    The boat is fun! Padded bench seats are on top of the cabin, so you get to comfortably ride up high. He brought ice and a cooler, and we just had to fill it. He also had a iPod docking station with bluetooth so we could play our own tunes.

    I would highly recommend an authentic experience boating with Chris who knows the ins and outs of the harbor islands and the people there.

  • Our family had a great day with Chris, which included exploring Lovells and Georges Islands, kayaking, stand up paddle boarding and cruising around Boston Harbor. Chris was pleasant, talkative, and his strong experience as a boat captain and knowledge of the surrounding area was apparent, particularly during the "Eco Tour" he gave us of Lovells Island.

    The boat is a sturdy, comfortable cruiser with multiple great spots to sit and enjoy the ride. We would recommend him to anyone looking to enjoy an entertaining and safe cruise.

Boat Location - Winthrop, MA, United States}